Ladies, have you ever wondered what you'd look dressed as (made up to look like) a man?

I have always wanted to do that and have never tried it. Thank you for the question. I’d like to think I’d make a rather handsome fellow.

I was Teddy Roosevelt one Halloween, and I was also a male hippy another Halloween. It mist have been successful as several folks thought I was male for real.

I don’t have the brow ridges to really look male. The best I can do is look like an effeminate, overweight shoe salesman.

Uh, no.

I’ve often thought I’d be better looking as a man. Especially with a moustache and beard.

Yes I have wondered that! I tried for a drag ball at the school where I’m studying right now, but I ended up in the “really butch dyke” category more than being even slightly passable as male. I wonder what would happen if someone who was actually talented at doing these sorts of things were able to do it for me…

Just spent forever looking for this great youtube video of the best drag king ever to no avail. Will keep searching!

I had short hair for a long time, from a cute pixie cut to almost buzzed. It was really cool that I could change how feminine I looked just by my choice of clothes, but always come across as somewhat androgynous.

My best friend and I sometimes got mistaken for guys if we wore baggy clothes. We wondered what things would be like if we had been born as boys, and we knew what boy names our parents would have chosen for us. (She would have been Damian; I would have been Andrew.) But I have olive skin and dark hair, and I tend to dress kind of emo. I’d probably look like Pete Wentz if I dressed as a guy. D:

I’ve tried it – I look awesome.

@Simone_De_Beauvoir I bet. :)

No. I have never thought of this, or being a man in any way. A relative of mine used to talk about how it is better to be man, she wishes she had been born a man, When she said it I realized I have never had that cross my mind (I was in my early 30’s when she said it).

I’ve dressed up as a guy for Halloween before, such as a punk rocker (it was all guys clothes, and I did it to resemble a friend of mine), bloody sailor, bloody football player (I was a creative child lol) I think when I dressed up in all my friends clothes was when I looked the most “masculine”.
I find it fun, and definitely interesting. But, nothing I’d want to do seriously. Oh, and I can just look at my son and see what I would look like as a boy..he looks a lot like me, and is quite feminine looking..but you can still tell he’s a boy (well, in my opinion you can..not in others)

I would not look good as a man. I’m short and have a curvy figure. Maybe I could pass as Napolean.

@tinyfaery I’ve got the same body type as you. I have petite, rather feminine looking features, as well. Perhaps, someone with a bit of talent could help me out and pull it off.

@jmah okay, there are pictures of this…a photographer took them…my best friend from high school (whose gender identity is pretty masculine usually) got dressed up all femme and 40’s flapper-like and I had a suit (obviously) and was being very ‘this is my lady’...I don’t think the photographer will let me have the jpg for fluther…boo

Yea. I didn’t like it lol

@Simone_De_Beauvoir Bummer. I wish that I could see them.

@Facade lol, you’d make a cute boy.

For me, I’d be more of an androgynous look. I’m not talking facial hair.

@jmah you should come over – my friends and I have all the supplies – also, I asked the photographer if I can have the pics sent to me as jpgs again?

@Simone_De_Beauvoir Ha, I wish that I could go over. I think that it’s a hot look, though. I find it interesting when you have someone with feminine features and they’re given an androgynous look. Very sexy.

Yup. So I tried on some of the manliest clothes I could find in my closet. I was a stud.

I’ve tried a couple times. I was a tomboy as a kid (and still kind of am, to a lesser degree) so I was always thinking about how I would be as a boy. My junior year in high school I went to prom in a tuxedo instead of a dress. It was awesome.

More recently, I had to dress as a boy since I was in an opera workshop performing the role of Cherubino (the pubescent, ultra-hormonal boy) in The Marriage of Figaro. My family, friends and teacher hardly recognized me, and my boyfriend said I pulled off being a boy scarily well. That amuses me.

The most important part of appearing masculine or androgynous is not in the clothing, but the way you hold yourself. Learning how to walk, stand, and make gestures like a boy were more important in my opera performance than the clothes I was wearing.

I would encourage you to try it out! Stepping into the shoes of the opposite sex gives you great perspective on yourself, not to mention cross-dressing has enormous potential for hilarious anecdotes.

The Wife dressed up like a Man for a Halloween Party we went to as a Gay Couple, all Adults were there and everyone thought I had converted and were fully sure when she went down and “Did me”. a few days later we divulged our secret!

Now I have James’ “Laid” and “Venus as a Boy” by Bjork in my head.

I’ve never thought of trying it. I pretty much lost my chance of passing for a boy when I was 12.

Found it!! This girl does a daaamn good job. Very jealous. Hell, all my roommates are gone tonight… maybe I’ll give it a try again!

Without make up on and my hair slicked back I look so much like my father, it’s scary.

@fireinthepriory She’s a pretty girl and she did a great job.

Girl, do it!

I dressed as Boy George for a Halloween party once- does that count??

For shits, I tried one of those online virtual hair sites. The first one that I pulled up had me looking like Adam Lambert, haha! Oy, vey!

Yes I have. It was really fun to be able to take up as much space as I wanted, swagger and be vocal without being looked down upon. Binding was a bitch though. Packing was cool- it felt fun and different.

I put on my ‘Renta suit and went out. Had to use some makeup to make my apple cheeks a bit less apparent and voila- man.

I was pretty damn hot if I do say so myself.

@gemiwing, what did you do about your voice?

@Jeruba- I have a fairly middle of the road voice anyway. I only sound girly when I talk to Hubbs. He’s the only one I talk to like that. So I just relaxed my throat a bit and ran with it. I think it helped that a lot of guys have middle/tenor/alto voices.

ETA- Plus I’m tall so that helped ‘sell’ the package. hurhur

Fascinating! Tell me more. What did you do with your hair? Did you change your eyebrows like the girl in @fireinthepriory‘s video? Did you add facial hair? Do you think you looked like an effeminate man? How did you manage to change your walk?—the walk is so unconscious that it is very hard to disguise.

@Jeruba-

Well with my hair- it was short at the time. I parted it on the upper side and just left it. I used to (girl mode) brush it all forward and maybe flip the front bangs up. I studied men’s hair styles and picked one. I’m Polish so I already have an oddly masculine hairline so I simply needed to accentuate it.

I didn’t add facial hair because it didn’t make sense for the look I was going for. A nice suit and a weird pornstache wouldn’t work together right. So I just used some makeup and created a very light shadow. I didn’t modify my eyebrows- I just didn’t get them waxed for a month and they filled in enough that I could simply darken them with a bit of eyeliner. Plus, metrosexuals were big then so it wasn’t too odd.

I don’t know if I looked effeminate or not. There aren’t any pictures either so I couldn’t really say. I suppose I could revisit the look and snap a pic of that. Lord knows if I could still fit in my suit now.

The walk was difficult but came easier than I thought it would. Honestly the thing that helped the most was packing. It’s easier to get the swagger when you have something to swing, as it were. It’s about moving your shoulders more and your hips less. I pictured my center of gravity lifting and being higher. Also binding helped as I no longer had to correct my posture for breasts.

I may have looked a hot mess, I don’t know. I like to think I looked awesome because I felt awesome. It was so much fun.

Thanks! That was great.

And so—how did women (and men) behave with you?

@Jeruba Same as now- but flipped. Men talked more and women talked less.

Waiting for @deni to respond…

I put my picture in the male option at yearbookyourself.com once, and I was shocked to see that I’m the spitting image of both my brother and grandpa with the right hair and clothes. Weird.

Just as I was about to post this last night Fluther decided it didn’t want to load for me, but here it is:

@jmah A little drag before bedtime is always a good idea. :)

I steered clear of looking like a butch lesbian this time, but ended up looking like a rather douchey version of my late father. Mindfuck!! I have uploaded a photo for your collective viewing pleasure. My 5 o’clock shadow didn’t show up too well, but all I had to work with was waterproof brown eyeliner, which doesn’t smear well. I also threw a photo of me up on the fluther photobucket to compare for those of you who don’t know what I look like. If I make it to another drag ball, I’m goin’ all OUT. :D

@fireinthepriory Wow- you look great! Love the attitude too.

I really like it. :)

Nikki and I decided that we’re going to give it a try. Although, she thinks that I’ll look like a “pretty brown-haired, blue-eyed boy”. I’ll be sure to post pictures here.

@fireinthepriory awesome, I’d do ya.

@tinyfaery Who says you have to be tall to dress in drag as a man? I’m short like you, but when I went to a Halloween party dressed as a male hippie, the chicks dug it. ;)

Thanks guys! It was much less passable if I smiled, hence my snarky grimace, haha.

@tinyfaery – how tall are you? my Wife is 5’ 4” and really pulls it off as a Man!

5’ 2”.

@tinyfaery I’ll just bet you looked Compact and Stately in the suit or whatever you wore!

Not really because I’ve got a male twin cousin.

@hungryhungryhortence How do you have a cousin that’s a twin?

@ParaParaYukiko She’s saying she and her male cousin look like twins, so she knows what she’d look like as a guy.

@ParaParaYukiko: He’s actually my 3rd cousin (mom’s maternal cousin’s son) and he and I have always looked alike since kids, we’re two days apart in age.
no, we don’t have the same dad

The girlfriend is going to give it a try tonight. She thinks that she’ll look just like her bro, lol. Maybe, I’ll post pictures.

Nikki gender bending.

@jmah woohoo

Haha, she tried.

@Simone_De_Beauvoir Wow. Nice avatar.

@jmah thank you :)

Damn! Girlfriend’s a hottie.

She is. :) I’m a lucky girl.

@jmah I like it! She looks glamorous. And kind of like a feminine Captain Jack Harkness, if that means anything to you.

I know how you’re talking about. The character from Dr. Who/Torchwood.

Yep! She looks kinda militaristic and old-fashioned and sexy. That combo always makes me think Captain Jack.

@jmah I love your girl’s eyes – beautiful and dreamy!

@fireinthepriory cute boy! =)

@titania thank-you. She has pretty light green eyes. She’s a keeper. :)

@titania Thanks! It’s fun, I recommend it to everyone. :)

Just randomly stumbled onto this question, months later..

I’ve wondered, but haven’t really had to wonder because one summer many moons ago it was quite hot in temperature and I just could not stand my hair any longer. So I marched down to the barber shop in the village (seemed a better fit for me than the ladies’ salon) and had the guy cut it all off. It was really short, like half an inch on top, spiked with product, and shaved around the sides and back. Basically, a dude’s cut. I totally did not care and I loved how easy it was and, of course, how much cooler I was without all the hair on my head.

This is when I came to realize that, without longer, femininely styled hair, I look like a boy. So much so that people would somehow completely not see my breasts (cause my head, face, and the rest of me looks so male) and think I was a guy. I got stopped from going into two different women’s restrooms, not to mention you would not believe the surprised looks I would get coming out of a stall if there was a woman at the sink!

I think it’s hot when girls dress in drag, so of course I’ve tried it. It’s just not all that satisfying to me personally, because I don’t look that much different from my normal self. ;)

(One of the few photos of the spiky hair, looks like it had grown in some)